6515-36-2

Usage

Uses

Used in Pharmaceutical Industry:
7-Hydroxyflavanone is used as a chiral compound for the stereoisomeric separation of flavonoids. This is achieved using polysaccharide-based chiral stationary phases in nano-liquid chromatography (nano-LC). The ability to separate stereoisomers is crucial in the development of pharmaceuticals, as different stereoisomers can have different biological activities and potencies.
Additionally, 7-Hydroxyflavanone and its derivatives have been studied for their potential use in drug discovery and development. Their diverse range of biological activities, including antioxidant, anti-inflammatory, and anticancer properties, make them promising candidates for the treatment of various diseases and conditions.

InChI:InChI=1/C15H12O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-8,14,16H,9H2/t14-/m0/s1

Upstream product

• 102-92-1 Cinnamoyl chloride 
• 108-46-3 recorcinol 
• 1776-30-3 (E)-2',4'-dihydroxychalcone 
• 21785-09-1 7-methoxyflavanone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 100-52-7 benzaldehyde 
• 140-10-3 (E)-3-phenylacrylic acid 
• 1776-30-3 2',4'-dihydroxychalcone 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 76240-27-2 7-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 98-80-6 phenylboronic acid 
• 76240-23-8 3-(3-Hydroxyphenoxy)propanenitrile 
• 126686-33-7 7-Methoxymethoxy-2-phenyl-chroman-4-one 
• 59887-89-7 7-hydroxy-4H-chromen-4-one 

Downstream Products

• 53258-99-4 7-hydroxy-8-(3-methylbut-2-en-1-yl)-2-phenylchroman-4-one 
• 78045-71-3 7-(γ,γ-dimethylallyloxy)flavanone 
• 866141-85-7 7-hydroxy-6-C-prenylflavanone 
• 59920-27-3 7-hydroxy-6,8-di-C-prenylflavanone 
• 89840-30-2 7-(2,3-trans-3,4-cis-3-hydroxyflavan-4-yloxy)flavanone 
• 6665-86-7 7-hydroxyflavone 
• 1776-30-3 (E)-2',4'-dihydroxychalcone 
• 38481-95-7 7-hydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran 
• 2430-55-9 7-ethoxy-carbonylmethoxyflavanone 
• 1154-77-4 2',4'-dimethoxychalcone 
• 82416-18-0 2',4'-diacetoxychalcone 
• 138166-64-0 7-hydroxyflavanone-7-O-β-D-glucoside 
• 89840-31-3 7-(2,3-trans-3,4-cis-3-hydroxyflavan-4-yloxy)-2,4-cis-flavan-4-ol 
• 89840-32-4 7-(2,3-trans-3,4-cis-3-hydroxyflavan-4-yloxy)-2,4-trans-flavan-4-yl phenyl sulphone 

Relevant academic research and scientific papers

Design, synthesis, and cholinesterase inhibition assay of liquiritigenin derivatives as anti-Alzheimer's activity

The marine environment is a rich resource for discovering functional materials, and seaweed is recognized for its potential use in biology and medicine. Liquiritigenin has been isolated and identified from Sargassum pallidum. To find new anti-Alzheimer's activity, we designed and synthesized thirty-two 7-prenyloxy-2,3-dihydroflavanone derivatives (3a-3p) and 5-hydroxy-7-prenyloxy-2,3-dihydro-flavanone derivatives (4a-4p) as cholinesterases inhibitors based on liquiritigenin as the lead compound. Inhibition screening against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) indicated that all synthesized compounds possessed potent AChE inhibitory activity and moderated to weak BuChE inhibitory activity in vitro. Kinetic studies demonstrated that compound 4o inhibited AChE via a dual binding site ability. In addition, all compounds displayed the radical scavenging effects. Finally, the molecular docking simulation of 4o in AChE active site displayed good agreement with the obtained the pharmacological results.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

Design, Synthesis, and Potential Antidepressant-like Activity of 7-prenyloxy-2,3-dihydroflavanone Derivatives

A series of 7-prenyloxy-2, 3-dihydroflavanone derivatives were synthesized and screened for their antidepressant-like activity. Among them, it was observed that compounds 5j and 5k were found to be the most antidepressant-like activity. In addition, it was found that compounds 5j and 5k significantly increased the concentrations of the main neurotransmitters 5-HT and NE in the hippocampus, hypothalamus, and cortex. Compounds 5j and 5k also significantly increased the contents of 5-HIAA in the hippocampus and cortex, shut down 5-HT metabolism compared with mice treated with stress vehicle. These results suggested that compounds 5j and 5k displayed potent antidepressant-like properties that were mediated via neurochemical systems.

Fast and efficient synthesis of flavanones from cinnamic acids

A fast and efficient synthesis of flavanones from cinnamic acids in three steps has been developed. First, the cinnamic acid was converted to cinnamyol chlorides using SOCl2. The acid chlorides were then treated with substituted phenols in BF3· OEt2to furnish corresponding chalcones in 42(75% yields. Base-catalyzed cyclization of the chalcones at room temperature afforded corresponding flavones in 85–95% yields. The conversion of the cinnamic acid derivatives to corresponding chalcones was found to be sensitive to the position and nature of the substituents on the aromatic rings.

Synthesis of flavanones using methane sulphonic acid as a greencatalystand comparision under different conditions

Flavonoids are an important class of natural products with wide range activities. Flavonoids includes flavone, flavanone, flavane & flavanol. The synthetic route invovles synthesis of chalcone followed by ring closing to give flavanone. So many catalysts were mentioned in past literature. But most efficient catalyst is methane sulphonic acid.It is easy to handle,less reaction time &easily available. Flavanones were synthesized from chalcone using methane sulphonic acid under thermal condition, microw wave and ultrasound condition.Flavanones are syntheisized in very less time compared to other conditions.

Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to heterocyclic acceptors

Flava Flavanone: Asymmetric conjugate additions to chromones and 4-quinolones are reported utilizing a single catalyst system formed in situ from Pd(OCOCF3)2 and (S)-tBuPyOX. Notably, these reactions are performed in wet solvent under ambient atmosphere, and employ readily available arylboronic acids as the nucleophile, thus providing ready access to these asymmetric heterocycles (see scheme).

Asymmetric cyclization of 2′-hydroxychalcones to flavanones: Catalysis by chiral Bronsted acids and bases

The asymmetric cyclization of 2′-hydroxychalcones to flavanones is a basic, enzyme-catalyzed step in the biosynthesis of flavonoid natural products, but poses a long-standing problem for asymmetric catalysis with small molecule catalysts. Earlier claims concerning the realization of an asymmetric flavanone synthesis by means of camphorsulfonic acid as chiral Bronsted acid catalysts were reinvestigated using accurate HPLC methods for quantification of enantiomer ratios. The previous claims of asymmetric induction were thus shown to be untenable. On the other hand, cinchona alkaloids serve as chiral Bronsted base mediators for the asymmetric cyclization of either 6′-substituted 2′-hydroxychalcones or 2′,6′- dihydroxychalcones. 2′,6′-Dihydroxy-4,4′-dimethoxychalcone, for instance, cyclized to give the naturally occurring naringenin-4′,7- dimethyl ether in up to 64 % ee at 81 % conversion. The catalysis shows a marked dependency of the enantiomeric excess of the product on the catalyst, solvent and reactant concentration. Based on these successful examples of asymmetric cyclizations of 2′-hydroxychalcones to flavanones, requirements for more active asymmetric catalysts can be defined. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones

We describe a facile efficient, and preparative approach for monohydroxyflavanone syntheses. Using this protocol, a hydroxyl is regio-selectively introduced at one carbon of a flavanone A- or B-ring per synthesis. The seven possible isomers were each synthesized from the corresponding monomethoxymethoxylated 2′-hydroxychalcones in acidic solution. These monohydroxyflavanones were characterized using a gas chromatography-mass spectrometry (GC-MS) system that incorporated a DB-5 capillary column. Ours is the first report of a preparative synthetic method during which a single hydroxyl can be selectively added to a flavanone A- or B-ring at any position. We are also the first to develop a procedure that separates the seven isomers by GC and characterizes the mass spectra of the isomers. Both the synthetic method and the GC-MS conditions may become important tools during future flavanone metabolism and oxidation studies.

Synthesis of flavanones using nanocrystalline MgO

The design and development of a truly nano heterogeneous catalyst for the Claisen-Schmidt condensation (CSC) of benzaldehydes with 2-hydroxyacetophenone to yield substituted chalcones followed by isomerization to afford flavanones with excellent yields and selectivity is described.

Flavonoids: Structural requirements for antiproliferative activity on breast cancer cells

Several classes of flavonoids (flavones, flavanones, 2′-hydroxychalcones and flavan-4-ols) having a variety of substituents on A ring were investigated for their antiproliferative activity against MCF-7 human breast cancer cells. Structure-activity relationships of these compounds were discussed. 2′-hydroxychalcones and methoxylated flavanones were found to be potent inhibitors of MCF-7 cells growth whereas flavones and flavan-4-ols appeared to be weak inhibitory agents except 7,8-dihydroxyflavone.